Identification of polymorphism in ethylone hydrochloride: synthesis and characterization

Maheux, Chad R.; Alarcon, Idralyn Q.; Copeland, Catherine R.; Cameron, T. Stanley; Linden, Anthony; Grossert, J. Stuart

doi:10.1002/dta.1859

Cited by 13 publications

(18 citation statements)

References 40 publications

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“…Compound 3 can be classified as 3,4‐methylenedioxy and N ‐monoalkylcathinone. The possible fragmentations of this kind of cathinone were the loss of water, the loss of CH 2 O from the 3,4‐methylenedioxy group, CO loss that followed water loss and the loss of methyl radical . For the N ‐monoalkyl cathinone subclass, we detected fragments resulting from the loss of amine groups at m / z 135.0438 and 149.0231 (Figure A, peaks d, e).…”

Section: Resultsmentioning

confidence: 94%

Analytical characterization of three cathinone derivatives, 4‐MPD, 4F–PHP and bk‐EPDP, purchased as bulk powder from online vendors

Apirakkan

Frinculescu

Shine

et al. 2017

Drug Testing and Analysis

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Novel emerging drugs of abuse, also referred as new psychoactive substances, constitute an ever-changing mixture of chemical compounds designed to circumvent legislative controls by means of chemical modifications of previously banned recreational drugs. One such class, synthetic cathinones, namely β-keto derivatives of amphetamines, has been largely abused over the past decade. A number of new synthetic cathinones are detected each year, either in bulk powders/crystals or in biological matrices. It is therefore important to continuously monitor the supply of new synthetic derivatives and promptly report them. By using complementary analytical techniques (i.e. one- and two-dimensional NMR, FT-IR, GC-MS, HRMS and HPLC-UV), this study investigates the detection, identification and full characterization of 1-(4-methylphenyl)-2-(methylamino)pentanone (4-methylpentedrone, 4-MPD), 1-(4-fluorophenyl)-2-(pyrrolidin-1-yl)hexanone (4F-PHP) and 1-(1,3-benzodioxol-5-yl)-2-(ethylamino)-1-pentanone (bk-EPDP), three emerging cathinone derivatives.

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Section: Resultsmentioning

confidence: 94%

Analytical characterization of three cathinone derivatives, 4‐MPD, 4F–PHP and bk‐EPDP, purchased as bulk powder from online vendors

Apirakkan

Frinculescu

Shine

et al. 2017

Drug Testing and Analysis

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“…Finally, 3,4-methylenedioxyphenyl-1,2-propanedione and an imidazolium by-product, which have been previously identified as organic impurities in synthetic cathinones, [14,19] were not identified in the synthesized methylone. 3,4-Methylenedioxyphenyl-1,2propanedione may form by decomposition of methylone under a variety of conditions.…”

Section: Synthesis Of Methylonementioning

confidence: 91%

“…products showed that methylone was the principle component, [8,9,11] with impurities 11, 12, 13 and 15 consistently identified and impurity 14 detected in two preparations. [19] Impurities 12-14 were known potential reaction by-products of the amination reaction. Impurity 11 was carried over unchanged from the previous reaction product although it might have also been formed from the decomposition of methylone.…”

Section: Synthesis Of Methylonementioning

confidence: 99%

“…Impurity 11 was carried over unchanged from the previous reaction product although it might have also been formed from the decomposition of methylone. [19] Impurities 12-14 were known potential reaction by-products of the amination reaction. [2,32] Impurity 12 was formed through the reaction of the ketone functional group of 3,4-methylenedioxypropiophenone and methylamine, as shown in Figure 12.…”

Section: Synthesis Of Methylonementioning

confidence: 99%

“…[7] The vast majority of chemical analysis for synthetic cathinones has focused on characterization and structural elucidation, including the analysis of methylone. [8][9][10][11][12][13] There have been few reports of the organic impurity profiling of synthetic cathinones, [14][15][16][17][18][19] presumably as these psychoactive substances (NPS) are relatively new to the recreational drug market. Organic impurities are typically identified by gas chromatographymass spectrometry (GC-MS), [20] however, structural elucidation can also be aided via nuclear magnetic resonance (NMR) spectroscopy.…”

Section: Introductionmentioning

confidence: 99%

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Organic impurity profiling of methylone and intermediate compounds synthesized from catechol

Heather

Bortz

Shimmon

et al. 2017

Drug Testing and Analysis

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This work examined the synthesis and organic impurity profile of methylone prepared from catechol. The primary aim of this work was to determine whether the synthetic pathway used to prepare 3,4-methylenedioxypropiophenone could be ascertained through analysis of the synthesized methylone. The secondary aim was the structural elucidation and origin determination of the organic impurities detected in methylone and the intermediate compounds. The organic impurities present in the reaction products were identified using GC-MS and NMR spectroscopy. Six organic impurities were detected in 1,3-benzodioxole and identified as the 1,3-benzodioxole dimer, 1,3-benzodioxole trimer, [1,3] dioxolo[4,5-b]oxanthrene, 4,4'-, 4,5'-, and 5,5'-methylenebis-1,3-benzodioxole. Six organic impurities were detected in 3,4-methylenedioxypropiophenone and identified as (2-hydroxyphenyl) propanoate, [2-(chloromethoxy) phenyl] propanoate, (2-propanoyloxyphenyl)propanoate, 5-[1-(1,3-benzodioxol-5-yl)prop-1-enyl]-1,3-benzodioxole, (5E)- and (5Z)-7-(1,3-benzodioxol-5-yl)-5-ethylidene-6-methyl-cyclopenta[f][1,3]benzodioxole). Exploratory synthetic experiments were also conducted to unambiguously identify the organic impurities detected in 3,4-methylenedioxypropiophenone. Two organic impurities were detected in 5-bromo-3,4-methylenedioxypropiophenone and identified as [2-(chloromethoxy)phenyl] propanoate and 3,4-methylenedioxypropiophenone. Five organic impurities were detected in methylone and identified as 3,4-methylenedioxypropiophenone, 1-(1,3-benzodioxol-5-yl)-N-methyl-propan-1-imine, 1-(1,3-benzodioxol-5-yl)-2-methylimino-propan-1-one, 1-(1,3-benzodioxol-5-yl)-N1,N2-dimethyl-propane-1,2-diimine and butylated hydroxytoluene. The origin of these organic impurities was also ascertained, providing valuable insight into the chemical profiles of methylone and the intermediate compounds. However, neither the catechol precursor nor the 1,3-benzodioxole intermediate could be identified based on the organic impurities detected in the synthesized methylone using standard techniques. This demonstrated that the organic impurity profiling of methylone had limitations in the determination of precursor chemical and synthetic pathways used. Copyright © 2017 John Wiley & Sons, Ltd.

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Dehydration‐fragmentation mechanism of cathinones and their metabolites in ESI‐CID

et al. 2020

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Various cathinone‐derived designer drugs (CATs) have recently appeared on the drug market. This study examined the mechanism for the generation of dehydrated ions for CATs during electrospray ionization collision‐induced dissociation (ESI‐CID). The generation mechanism of dehydrated ions is dependent on the amine classification in the cathinone skeleton, which is used in the identification of CATs. The two hydrogen atoms eliminated during the dehydration of cathinone (primary amine) and methcathinone (secondary amine) were determined, and the reaction mechanism was elucidated through the deuterium labeling experiments. The hydrogen atom bonded to the amine nitrogen was eliminated with the proton added during ESI, in both of the tested compounds. This provided evidence that CATs with tertiary amine structures (such as dimethylcathinone and α‐pyrrolidinophenones [α‐PPs]) do not undergo dehydration. However, it was shown that the two major tertiary amine metabolites (1‐OH and 2″‐oxo) of CATs generate dehydrated ions in ESI‐CID. The dehydration mechanisms of the metabolites of α‐pyrrolidinobutiophenone (α‐PBP) belongs to α‐PPs were also investigated. Stable‐isotope labeling showed the dehydration of the 1‐OH metabolite following a simple mechanism where the hydroxy group was eliminated together with the proton added during ESI. In contrast, the dehydration mechanism of the 2″‐oxo metabolite involved hydrogen atoms in three or more locations along with the carbonyl group oxygen, indicating that dehydration occurred via multiple mechanisms likely including the rearrangement reaction of hydrogen atoms. These findings presented herein indicate that the dehydrated ions in ESI‐CID can be used for the structural identification of CATs.

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Identification of polymorphism in ethylone hydrochloride: synthesis and characterization

Cited by 13 publications

References 40 publications

Analytical characterization of three cathinone derivatives, 4‐MPD, 4F–PHP and bk‐EPDP, purchased as bulk powder from online vendors

Analytical characterization of three cathinone derivatives, 4‐MPD, 4F–PHP and bk‐EPDP, purchased as bulk powder from online vendors

Organic impurity profiling of methylone and intermediate compounds synthesized from catechol

Dehydration‐fragmentation mechanism of cathinones and their metabolites in ESI‐CID

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